


Running to the Edge of the World

by sakuranomi808



Category: Supernatural
Genre: Explicit Language, Explicit Sexual Content, Frottage, M/M, Masturbation, Sex Toys, Weecest
Language: English
Status: Completed
Published: 2020-12-31
Updated: 2020-12-31
Packaged: 2021-03-11 02:26:29
Rating: Explicit
Warnings: Underage
Chapters: 1
Words: 2,252
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/28447629
Author URL: https://archiveofourown.org/users/sakuranomi808/pseuds/sakuranomi808
Summary: Dean gets a new toy for him and Sam to experiment with and it turns out to be awesome! Sam is still really young in this; they are about 13/17 here.
Relationships: Dean Winchester/Sam Winchester
Comments: 4
Kudos: 234





	Running to the Edge of the World

**Author's Note:**

> Sorry, my timeline is jumping all over the place, but this takes place shortly after my other fic "Then Again, Privacy is Overrated". Inspired by a suggestion by an Anon commenter: "the boys are tip-to-tip inside a more tubular toy so that it rubs back and forth, down one and up the other". I am really easily influenced, so thanks Anon for the wonderfully dirty idea!

Sure, the place was shady as hell, but there was no way they’d let Sam -- who looked every bit like the young teen that he was -- into the store. And so Sam waited back at the motel like a kid on Christmas morning, and Dean sucked it up and went back to the shop by himself like the world’s perviest Santa Claus ever. The same chick was working the register as the last time, and Dean thought maybe she recognized him, but she didn’t say anything, just flirted with him and made a comment about how a good looking kid like him shouldn’t have any trouble finding a real pussy to fuck. 

Dean hightailed it out of there as soon as he’d made the purchase, certain that his face was as red as a tomato and thankful that he’d worn a longer coat to hide the obvious erection pressing against the back of his zipper. He slammed the motel room door behind him, shaking off the chill of winter as he shrugged out of his jacket and set the brown paper bag down on the table where Sam was doing a terrible job of pretending to study. 

“Did you get it?” Sam asked, already a little breathless as he shifted in his chair. 

“Yep, I did,” Dean replied. “Did you finish all your homework?” 

“Uh huh.” Sam’s eyes were glued to his brother’s hands as Dean opened the bag and pulled out the toy.

“Are you sure? Cause you look kinda distracted to me,” Dean said, admittedly a bit amused at the fact that his kid brother was practically salivating at the sight of the cock-sleeve. He took his pocket knife out and began to carefully cut away at the plastic packaging.

“C’mon Dean,” Sam huffed. “Of course I’m distracted. I’ve been on edge all afternoon, just waiting for you to come back.” 

It wasn’t completely surprising. After all, Dean remembered how horny he’d been at that age, just starting to figure out what his dick was for, his brain constantly fixated on when and how to get his hands on it next. Sam was lucky that he had such an awesome big brother to help him figure all of this stuff out; that’s what Dean had mostly convinced himself, anyway. 

Dean just grinned and gave Sam the slightest, barely there-nod, but it was enough for Sam to move over to the bed, unzipping his pants and shoving them, along with his briefs, down and off. He wasn’t kidding about being hard -- his cock was stiff and leaking, the swollen head all dark and shiny where a drop of pre-come was oozing from the slit. Dean knew that Sam was sort of insecure about his size, but the truth was that he had a decently sized dick already, especially at his age. Dean hurriedly stripped down to just his boxers and joined his brother where Sam was now sitting at the center of the bed, looking expectantly up at Dean.

It wouldn’t be the first time they had masturbated together, but the promise of a new toy to experiment with was as thrilling as it was terrifying. It was a slippery slope; Dean was well aware of that, but he chose to believe that this was what was best for his little brother. Plus, he couldn’t stand the thought of anyone else touching Sam, making him feel good the way that only Dean was capable of. Dean grinned when Sam reached out and impatiently shoved at the waist of his boxers and his hard, swollen flesh sprang free, whacking against his own belly. 

Sam pulled out a bottle of lube and flicked the cap open, licking his lips as he drizzled some of the liquid along the length of Dean’s erection. The sensation of Sam’s hands on him sent a fresh rush of blood down to Dean’s already achingly hard cock. There was just something about Sam’s slender fingers, the soft press of his palms, the reverent way in which he touched Dean that sent shivers racing up and down his spine. 

Dean grabbed the lube and carefully prepped his brother as well, smoothing the slick, shiny liquid along Sam’s shaft and up around the swollen crown. Sam was trembling already, eyes fluttering shut at the sensation of Dean’s touch, so he forced himself to pull his hands away, busying himself instead with inspecting their new toy. 

It was made of soft, clear plastic, unlike the rubbery flesh colored pocket-pussy that Dean had not-so-subtly introduced Sam to just a few weeks ago; cylindrical shaped and open on both ends, with little rounded nubs all along the inside. It looked pretty weird honestly, but Dean couldn’t wait to get his dick inside it.

“Up on your knees, Sammy,” Dean quietly instructed as he did the same, the two of them now facing each other. Pushing his erection down a bit so that it was at the same level as Sam’s, he unconsciously held his breath as he thrust into the sleeve and guided his brother’s cock into the other end. 

Sam moaned softly, voice catching in his throat as he sunk deeper into the toy, all the way until the tip of his cock bumped against Dean’s at the center of the tube. “Oh God,” Sam breathed. “It feels really good.” 

Dean nodded, breathless as well as he tried desperately to quell the pleasure pooling in the pit of his stomach. This was quite possibly the most intimate thing they’d ever done, the two of them sharing this pleasure, their cock-heads pressed together as Dean carefully slid the toy all the way to the base of his shaft, and then toward Sam, and back again. 

“Oh God,” Sam repeated as Dean began to slide the sleeve back and forth between them, a slow and steady rhythm that was sending sparks of pleasure through every inch of his body. 

Dean lowered his gaze between them and gasped at the incredibly arousing sight: They were both hard-as-nails, their dark, blood-thick flesh clearly visible through the mostly see-through sleeve. The hottest thing about it was that their dicks were touching, which was like the one unspoken rule that they’d both decided to follow up until this very moment. The rhythmic sound of their slick, heated flesh fucking in and out of the toy over and over again was way more arousing than it had any right to be.

“Dean, slow down,” Sam pleaded. “I’m so close, I’m-” 

The words had barely escaped Sam’s lips before his body seized and jerked and Dean felt his brother’s come flood the space between them, hot and slick and perfect as it shot out against Dean’s swollen tip again and again. Through some unimaginable feat of self-control, Dean managed to hold off his orgasm and continue to work the toy over his brother’s cock as Sam rode out his climax. Sam was gorgeous like this, with his mouth falling open and his eyes slamming shut, his breaths ragged as a visible shiver ran through his body. Dean waited for his brother’s content sigh before he carefully slipped the sleeve off of both of them and let out his own shaky breath. 

“Ugh,” Sam blurted out, surprising Dean a bit. 

“Not good?” Dean frowned. 

“Too good.” Sam sighed as he sat back on his haunches, looking adorably miserable. 

Dean tried to talk himself out of it for a second before he leaned in and brushed his lips over Sam’s pout. Sam gasped, blinking hard and silently searching Dean’s eyes with about a million unspoken questions that Dean didn’t have the answers to. Instead, Dean asked, “Did you ever kiss anyone before, Sam?”

Sam shook his head, his eyes wide and his chest rising and falling with quickening breaths. With a surge of possessiveness, Dean lunged forward, meeting Sam in the middle as their lips came crashing together again, open-mouthed and needy, tongues instantly battling for control. Sam gave in first of course, willingly letting his brother dip his tongue into his mouth, where Dean eagerly explored for a few moments. 

The fact did not escape him that he was now making out with his kid brother and this one kiss with Sam far surpassed any other that Dean had ever shared with anyone else. It should’ve been weird, but inexplicably it was like nothing else in their lives made sense except for this. 

When Dean finally had to pull away with a quiet gasp for breath, he stretched his legs out and then guided Sam to sit down again, facing him with his legs draped over Dean’s hips. There was barely an inch of space between them now, and not surprisingly Sam was hard again, his cock standing up straight against Dean’s, just a bit shorter and more slender. 

“What’re you doing?” Sam’s pupils were blown wide and his lips were kiss-bitten and pink, stands of sweaty hair sticking to his forehead -- looking utterly and totally debauched in the best possible way. 

“Think we can both fit in this thing?” Dean asked instead of responding. He gave his brother a small smile and gestured for him to come closer. 

Sam breathed out something that sounded like “Ohhh,” as he scooted closer until their balls were literally pressed together. Dean curled his big hand around their shafts and positioned the sleeve over them both. 

Dean couldn’t help muttering a choked-off obscenity as Sam’s come started to ooze out of the toy, dripping down to wet both of their stiff lengths. Sam hadn't even been old enough to ejaculate when they first started fooling around like this, just shuddered through mostly dry orgasms for a while. But then, he’d started to leak a thin, watery liquid when he climaxed, and just a short while later he was shooting like a geyser when he came, just like Dean. He felt an oddly placed sense of pride in how quickly his little brother was growing up. 

“That’s so hot,” Dean breathed. “Look at all of your come dripping out.” 

Sam’s cheeks flushed pink in response, but he didn’t say anything, just caught his lip between his teeth and tentatively reached between them to help Dean guide the sleeve further down. They both moaned at the slick, too-tight drag of friction as it slowly encased both of them. Once it was resting snugly at the base of their cocks, Dean let out a shaky breath and raised his eyes to meet Sam’s. 

“How does that feel?” 

“So tight,” Sam mumbled. “It’s really good.” 

It felt fucking incredible, but it wasn’t just the toy. Dean could feel every inch of his brother’s cock throbbing against his own, even the tiniest of movements between them sending sparks of pleasure racing through him. He hummed in agreement and reached up to cup Sam’s cheek, thoughtfully sliding his thumb along his bottom lip before leaning in for another kiss. 

They continued to make out as Sam curled his arms around Dean’s shoulders and Dean naturally took control of sliding the sleeve over their cocks. He knew he wasn’t going to last long, had been balanced precariously on the edge for too long, but a part of him didn’t ever want this to end -- wanted to hold on to this moment with Sam forever if he could. 

“I’m close, Sammy,” Dean said, finally breaking away and letting his gaze fall down between them. “Jesus,” he breathed as he drank in the sight of their red, leaking cock-heads peeking through the top of the sleeve on every down-thrust. “I’m gonna come. Come with me?” he pleaded, desperately wanting Sam to fall over the edge at the same moment, the same way they’d somehow managed to come together several times before. 

Sam cried out Dean’s name as he clutched at his brother’s shoulders, his cock swelling and jerking against Dean’s as his climax tore through him. That was all it took really, knowing that he was giving Sam the pleasure that no one else could, that no one else ever would. Dean came hard with a groan, thrusting up into the sleeve as the first spurt of his release shot out so hard that it landed on Sam’s collarbone. He worked them both through it, feeling like he was almost having an out-of-body experience as he watched their dicks shooting over and over again, painting the space between them in sticky-hot come as the pleasure washed over him in waves. 

Finally, Sam leaned forward, sighing contentedly as he rested his forehead against the crook of Dean’s neck. A small but strong after-shock ran through Dean’s body as he pulled the toy off of their softening flesh before the sensations could become too much. Sam was almost completely boneless at this point, resting most of his weight against Dean’s chest as Dean set the sleeve down on the mattress beside Sam’s hip.

“You all right?” Dean chuckled. 

“I need a shower,” Sam mumbled into Dean’s shoulder. “And a nap. Maybe not in that order.” 

Dean outright laughed at that, his body still thrumming pleasantly all over. “Want some company?” he asked, his smile widening at his brother’s nod. “I’ll make sure you don’t fall asleep in there.” 

Before Sam could pull away, Dean slid a hand up to thread through the too-long hair at the back of his brother’s head and inhaled deeply against his temple, soothed by his familiar scent and the feeling of Sam’s heart beating slow and steady against his own.


End file.
